Ann: a Love Story

© 2025, All rights reserved -- mimaster

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I should have been tired when I woke up. It had been another late night, and I had gotten very little sleep. But I woke up feeling refreshed and alive. My first thought was of Ann. I was excited about her being at Matt's and getting a chance to talk to her. I was more excited that she had seemed to be interested enough in me to openly flirt. And I was ecstatic that I would be seeing her again that evening. Suddenly, the weekend seemed like a distant memory.

I looked at the boxer's I'd dropped next to my bed after using them to clean myself up the before falling asleep. They were crusted and hard from the dried cum. I couldn't put them in the hamper in my bathroom, so I stuffed them under my bed for the time being and got up to take a shower. I usually did my own laundry, but every once in a while my mom would need some more clothes to finish out one of her loads, so she'd do mine. It wasn't often, but I wasn't going to take a chance.

On the way out of my room, I put them in a sports bag and headed down the hall. I had a habit of taking the bag with me a lot, and I often took it as I went to work, in case something came up and I didn't want to head home first. So it wouldn't be that unusual for me to carry it with me in the morning.

I had actually woken up early so I went and put the bag in the car, and went back in to make some breakfast. As I walked back into the house, Mom was standing in the kitchen, and she was surprised to see me.

"You're up early. I thought you got in late again last night."

"I did. I just woke up early, and I couldn't go back to sleep, so I got up. I feel pretty good, but I could sure use some coffee."

She poured me a cup and I sat down to have a bowl of cereal.

"You weren't playing basketball all night, were you?" she asked.

She wasn't being nosy. She could be, but she wasn't all the time. She just hadn't seen me in a while, and she rarely had company with her in the morning, since dad and I tended to run out as soon as we were ready.

"No. We played a couple of hours. I was up late talking to an old friend from school. She came back for the reunion. I wanted to find out how it went."

"I thought you wanted to avoid it."

"I did avoid it. That doesn't mean I don't want to know if I was the only loser in our class."

"Neil, stop talking like that! We've talked about that. You have too --"

I laughed and said, "Relax, Mom. I was kidding. It was just nice to see her, and to actually talk to someone my age."

"Who was it?"

"Ann Franklin. I'm not sure you remember her. She didn't hang out after school much."

"Sure I do. She's Marlin and Jean's girl. She was really cute, if I recall," she said, always trying to make a match. I think just to get me out of the house.

"Actually, she's gone from cute to gorgeous, unlike a lot of girls in our class. She's spent her ten years becoming a babe. She also lives in California, so calm down."

Mom smiled. She was happy to see me in a good mood for once.

I slipped out the door and headed to work, once again escaping any questioning about the weekend. With Ann in her mind, that was a distant event. And Ann had the same effect on me.

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The morning went very smoothly. Dad came in to say hi, and he made some small talk about my seeing a schoolmate. As usual, he had just enough information to be dangerous. I got him square on the details and he went his merry way.

The meeting he got put off the day before happened just after the morning break and it went very well. My boss was very enthusiastic, and I also got some great responses from the other department heads, as well as the President of the company. I walked away feeling good, but still knowing that there would be a large percentage of the company that wouldn't see things as they were. I was a just product of genes, and to them, it was all about who I was related to. I knew that shouldn't have bothered me, but it always did, even on my best days.

I got a phone call from Mark at S-T Incorporated about a half hour before lunchtime. His meeting with Harry, their VP, also went very well, and he was looking at a promotion. That, and Harry was so thrilled about finally winning the tournament between all those competitive companies, he was handing out bonus checks to all the players.

"I just put your check in the mail, buddy!"

"You didn't have to Mark. Believe me, I got well compensated while I was up there. You should have kept it."

"It's a check, Neil, not cash. Besides, I think you'll be glad I didn't."

"Why?" I said, thinking Harry was giving us something of a token monetary gift.

"It's for five hundred dollars, Neil."

"What? He shelled out five grand on the team?"

"Yeah... but it gets better. Come to find out, the big wigs from all of the companies in the tournament wager on the games. Harry told me yesterday that after seeing you and Dawn play together up the middle he went around and increased all his bets. He really cleaned up. He gave us half of what he won. I felt guilty about taking the money too, until he told me that."

With the mention of Dawn, I felt compelled to ask him some questions about his Sunday night and Monday morning. I didn't really want to, but I knew it would be worse if I never brought it up. I didn't want him to think I didn't appreciate his hospitality. And I didn't want him to think that everything we did was suddenly an issue. So, I asked about his time at the hotel.

"Denise was incredible, Neil. I can't believe she's forty-eight. You were right, she looks twenty years younger than that, and she fucks like it too. I think you and Dawn really just got her warmed up."

"Did you feed her?" I asked, concerned that they had forgotten.

"Besides the couple of loads she swallowed from me, and all the cum she drank from Jill?"

"Yes, dumbass... did she get a real meal?"

"Funny you should ask. When Jill and I opened the door, Denise was in the Jacuzzi. We thought she was in a bathing suit, but she got out naked and dried off, and then gave us each a big hug and a kiss. At that point, I thought we were going straight to the bed. But she said she was famished, and asked what we brought her to eat."

"You didn't take anything, did you?" I said disgustedly.

"No. Jill wanted to order room service. So I picked up the phone to call, and Denise told me to ask for Carlos. So I did, and when he got on the phone, Denise took it from me. She hung up the phone, and she was giddy and told us to hurry and get undressed."

"So, what happened?"

"Long story short, Denise was watching Jill ride me while she sat on my face. They were kissing each other, and there was a knock at the door, followed by a guy with a Hispanic accent announcing room service. Denise jumped off my face and ran to the door, yelling that her Latin lover was at the door."

"Wait, I thought I was the first guy she'd had since she got divorced."

"You were. Apparently, Carlos had been putting the moves on her since she went to work there. She'd been giving him the stiff arm because he's only twenty-five. But after you, she had time to think about what she'd been missing. I guess her ex ran off with a woman in her mid thirties, and she thought that outdoing him by ten years would really eat at him. So, she was going to let him make another move and give in."

"So what happened?"

"We did. He brought the food, but he was just beginning his shift, and he couldn't stop just to have fun. So, we had our fun with Denise first. We fucked her for hours. But Carlos showed back up about three in the morning, and he spent the night. The bed was plenty big enough for four."

"Did he fuck Jill?"

"Nah. She wanted to, and I would have let her. But he only had eyes and a cock for Denise. He couldn't get enough of her. I guess having to wait that long, he wasn't going to waste any time or any sperm on another woman. And that really made Denise happy. The fact that a twenty something guy could have fucked a smoking hot girl his own age, and he'd rather fuck someone twenty years older? That wasn't lost on her. I think it was sweet retribution for her husband running out on her."

"So, there wasn't a foursome?" I said, stating the obvious.

"Well, not technically. But there were four of us having sex, and there was one moment when I was fucking Jill while I was standing on one side of the bed, and she was on her back. Carlos was standing like I was, on the other side of the bed, fucking Denise doggy style. Denise looked down at Jill, and the next thing we know, they're kissing."

"Wow. That must have been cool."

"That's not even the best part. When Carlos and I came at about the same time, we each came inside our girls. As soon as we finished, Denise crawled to the other side and Jill and her got into a sixty-nine and ate each other. I never went soft watching that. After they made each other cum, Denise looked up from Jill's pussy and saw my cock in front of her face, so she started sucking me. And so Jill scooted out from under Denise, and she sucked Carlos."

"I thought you said that Jill didn't have sex with Carlos."

"No. You asked if she fucked him. She didn't. She only sucked Denise's juice off his cock. He was so turned on by watching Denise suck on me, after a couple of minutes, he wanted to change so he could fuck her again. I'm telling you Neil, those two are made for each other. Carlos can go forever, and Denise can really fuck. I don't know what her ex was thinking."

"That's what I thought too. I'm glad it worked out for all of you. Denise is a great woman. She deserves to be happy. So, when did you guys go home?"

"Well, I had to go to work, so we left about six in the morning so I could go home and great ready. Jill didn't have to go in. She took the day off because of the tournament. So did Dawn."

Dawn and Jill... both with the day off. I was thinking about all of the dirty possibilities, considering how I'd left Dawn; tied up and naked on her bed.

"So, aren't you going to ask?" Mark said, snapping me out of my erotic daydream.

"Ask what?" I said, knowing he meant Dawn. He remained silent on the phone, unwilling to go on with our conversation until I asked the obvious. I either wanted to know, or I didn't, and he wasn't going to offer unless I asked.

Caving to my own internal peer pressure, I asked. I suppose deep down, I really needed to know that how I left Dawn was okay. I'm not sure if it was closure I was seeking out. It was more to turn to the next chapter of my life; I needed that loose end tied up. It turned out it already was tied up, which apparently was what Dawn wanted.

"Which one of you found Dawn?" I asked.

"We both did. She wasn't answering when we called for her, so we went down the hall together."

"Was she still --"

"Oh yeah. She didn't even try to get out. She didn't want to. You did her a huge favor, and you didn't even know it," he said laughing into the phone.

"What? How's that?"

"You tied her up, and you did it on your own. She didn't have to ask you."

"I'm not following you. I already knew that," I said, confused by what he was getting at.

"Well, there are a couple of things you need to know first," he said, his voice trailing off.

I feared the worst. Maybe Dawn was hurt, or maybe she was really a lesbian and just played along for me. Maybe she was an alien from another planet sent to heal me, or maybe everything we had done together was all just to give me a heart attack from all the secretive crap that Mark seemed to be alluding to. Or maybe, just maybe, I was being an over reactive idiot.

"And they would be?" I said with trepidation rippling through my body.

"The first is, the hour that we swapped girlfriends, or whatever you and Dawn were --"

"Lovers," I quickly interjected.

"Right. When we swapped lovers, and I was with Dawn... we watched TV."

"What do you mean?"

"I mean, you and Jill were in our room doing what you were doing, and Dawn and I were on her bed watching TV."

"Porn?"

"No... a ballgame."

"Why? Why weren't you --"

"Because, I wanted to fuck Dawn, but she had established the 'no fucking' rule. She said at the time she was worried about our relationship, and mine with Jill, and hers with Jill. She was worried about all the things that might happen. I was looking at it as sex. I don't have any interest in her, really. But if we were going to go that far, then I didn't want any restrictions."

"Okay, so what happened?"

"Nothing. She knew my stance, I knew hers, and we agreed not to do anything, but we also agreed not spoil Jill's fantasy. And that brings me to the next thing you need to know."

"I'm scared to even ask what," I said, although the first hadn't been the earth shattering news I'd feared. Maybe he was letting me down easy.

He took a deep breath and said, "I don't suppose it's a shock to you that Jill and I watch a lot of porn. It was a novelty at first. We found a place where we could get VHS tapes, and it was so new to us that we got engrossed in it. What you were a part of was what that has eventually evolved into."

"What, the cabaret performances?"

"Yes," he said with a laugh.

"What about Dawn? Where does she fit into all of that?"

"She kind of stumbled into it. We thought we were alone one night, and Dawn came home early. We were too into it to stop watching, and she was intrigued, so she watched it with us. After that, we weren't so cautious about when we watched, and soon we were all getting together a couple of times a week. But we never did anything between the three of us."

I knew that Dawn had actually started watching porn with Jill first. At least, that's what she told me, and I refused to believe she would lie. Based on what Mark had just said, he thought Dawn had stumbled onto them together. And based on the conflicting stories, my guess was that Jill was playing them both to get her fantasies fulfilled. No matter, it was all done and out now, so mentioning it to Mark would only hurt feelings, and there was no point in that. Whatever happened after I'd left had him bursting with excitement as he told me.

"So we'd watch, and we would share what turned us on. You know, we'd share fantasies. The girls were into a lot more than I was, but that doesn't mean I didn't have any. So we would watch, talk about what we saw, and then Jill and I would go into our room and act something out that turned one of us on."

"What would Dawn do?"

"She masturbated. I felt bad about it, because she had things that turned her on just as much as Jill or I did, but she never got to live them out. That is, until you got here and she got to be Amanda to your Dean. But that was just one of a lot of fantasies she has from looking at those videos with us."

"Well, at least I got to help her live out that one," I said with some sort of pride.

"Two," he replied with a laugh.

"Two? You've lost me again, Mark."

"Well, we have almost fifty movies now. Some are total crap, but most of them are pretty good. We each have actors and actresses we're fond of, and we each have certain things that really get us going. And as you would think, for each of us it's different. Anyway, you saw the movie that the girls wanted to act out. It's one of their favorites."

"Yeah, I kind of gathered that. The beach scene was one of the hottest things I've ever seen!"

"Yeah, it was. And Dawn picked a scene out of that movie she wanted to do with you. But she has other scenes from other movies that have turned her on just as much, if not more."

"Really, like what?"

"Funny you should ask. There was one movie that starred the same actresses that were in the movie we watched that played Sophie and Amanda."

"What is it?"

"Well, the movie stars the blonde girl. She's in every scene of the movie. She's the heroine, I suppose, and in the movie, she plays an Heiress whose husband is in trouble with mobsters. I won't bore you with the whole plot, but at the beginning of the movie she's kidnapped by the mob in order to try and get her to talk about what her husband had been up to."

"Kidnapped?" I said, not really sure why that detail interested me.

"Uh-huh. So, they take her to this abandoned warehouse, and they strip her and tie her up almost exactly like you had Dawn tied on the bed. I mean, she was tied the same, but they had used ropes. Anyway, she's tied up, and they bring in this mob girl played by the Sophie actress, and she uses sex to her to try and get her to talk, making her cum over and over."

"So that's Dawn's fantasy? Being tied to the bed and made to cum?"

"Part of it; she actually fantasizes about being the Heiress in the

entire movie

. After that doesn't work on the bed, there's a scene in a bathtub, where the mob girl is spraying water on the Heiress's pussy to make her cum again. Then there's a lesbian scene where the mob girl makes her eat her out. She's got her hands tied behind her, and she's doing it in the middle of an office, under a desk while people are all around."

"That sounds interesting," I said, finding myself actually getting hard at my own desk. A flash of Dawn naked, with her hands tied behind her back, under my desk sucking on my cock went through my mind. I know it was a lesbian scene, but it was my desk, so it was suddenly my fantasy.

"Next, the mob girl threatens the Heiress, and she tells her that the only way to break her and get the needed information is to fuck it out of her. She holds a gun on the Heiress, and they bring in this stud that fucks her in all her holes and finally tit fucks her, cumming on her face. When that doesn't work, the mob girl jacks the guy off, making him cum on the Heiress's face a second time, and they tie her up naked outside of the Heiress's mansion covered with the cum as an example of what will happen to the families of guys that mess with the mob."

"So, what happened when you found Dawn?" I asked, wanting to know what part of the movie they may have acted out.

"Everything," he said laughing.

"Everything?"

"Yeah, everything. When Jill saw Dawn on the bed, she smiled at her, knowing Dawn had found herself in the same vulnerable position that the Heiress was in. Dawn and Jill locked eyes, and when Dawn had her attention, she looked over onto the floor near the closet. There, on the floor, was the blonde wig."

"Really?" I said, remembering that when Dawn took it off while playing Amanda for me, she threw it there as I came in her mouth after fucking her ass.

"Yes. Jill had me put it on Dawn, and she went into our room and got dressed in her outfit and her Sophie wig. I guess they acted out every scene in the movie, and Jill added some of her own to keep it going all day long."

"What do you mean, you guess?"

"I had to go to work, Neil. I didn't get to see most of it."

"Well, what part did you get to see?"

"The part where I came home from work, and Jill had the Heiress lying on our bed while she held my BB gun, pointing it at her. I walked into the living room, and Jill yelled for me to strip naked. I thought Dawn was out of the house, so I ran in to the room naked, and Jill told me I had to get the Heiress to talk. I was the last chance to protect the Mob and get the secrets she was withholding about her husband."

"So, you fucked her?"

"Every hole, Neil. I fucked her pussy, I fucked her ass, I fucked her face. I fucked her for well over an hour. Then I titty fucked her just like in the movie and I painted her face."

"Holy shit!"

"Yeah, holy shit. Dawn refused to talk, so Jill got me hard again and gave me this magnificent hand job, and I blew another load on her. She was dripping with my cum. Man, she looked hot."

"Wow, what a great ending, eh?"

"That's not how the movie ended. I told you, she gets tied up in front of her mansion as an example."